Method for preparing adamantyl unsaturated ester

An adamantyl and unsaturated technology, which is applied in the preparation of carboxylic acid halides, photosensitive materials for optomechanical equipment, coatings, etc., can solve the problem of reduced yield of adamantyl esters, which is unfavorable for large-scale production, and the purpose The problems such as the reduction of the yield of the product can be solved, and the effect of easy operation of the reaction process, fast reaction speed and improved conversion rate can be achieved.

Inactive Publication Date: 2010-10-27
HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above methods have the following disadvantages: 1. There are many reaction steps, which are easy to produce by-products, and as a result, the yield of the target object is significantly reduced; In the case of raw materials, the dehydration reaction of alcohol occurs preferentially, so that the yield of product adamantyl ester is significantly reduced
3. The experimental conditions are cumbersome and difficult to control, which is not conducive to large-scale production

Method used

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  • Method for preparing adamantyl unsaturated ester

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Preparation of ethylene glycol diester of acrylate-1-adamantanecarboxylate

[0040] After adding 2g of hydroxyethyl acrylate, 2.6g of triethylamine and 100mL of dichloromethane into a three-necked flask with a mechanical stirring device, the reaction temperature was 0-5°C, and 4.1g of 1-adamantanecarbonyl chloride was weighed, Then dissolve it in 40mL of dichloromethane, drop it into a three-necked flask within 3 hours, after the dropwise addition, continue to stir for 5 hours, let it stand overnight, and filter it with suction to obtain a light yellow liquid, which is washed with dilute hydrochloric acid solution (1mol / L), NaHCO 3 (1mol / L) solution and distilled water to wash the light yellow liquid (retained liquid is the upper layer), and use anhydrous Na 2 SO 4 Dry, filter, and remove the solvent to obtain a light yellow acrylic acid-1-adamantanecarboxylic acid ethylene glycol diester solid, whose structural formula is as follows

[0041]

[0042] Ethylene gl...

Embodiment 2

[0044] Preparation of ethylene glycol diester of acrylic acid-3-formyl chloride-1-adamantanecarboxylate

[0045] After adding 2g of hydroxyethyl acrylate, 2.6g of triethylamine and 100mL of dichloromethane into a three-necked flask with a mechanical stirring device, the reaction temperature is 0-5°C, and weigh 5.4g of 1,3-adamantanedi formyl chloride, and then dissolved in 40mL of dichloromethane, drop it into the three-necked flask within 3 hours, after the dropwise addition, continue to stir for 5 hours, let it stand overnight, and filter it with suction to obtain a light yellow liquid, which is washed with dilute hydrochloric acid Solution (1mol / L), NaHCO 3 (1mol / L) solution and distilled water to wash the light yellow liquid (retained liquid is the upper layer), and use anhydrous Na 2 SO 4 Dry, filter, and remove the solvent to obtain a light yellow acrylic acid-3-formyl chloride-1-adamantanecarboxylic acid ethylene glycol diester solid, whose structural formula is as fo...

Embodiment 3

[0049] Preparation of ethylene glycol diester of methacrylic acid-1-adamantanecarboxylate

[0050] After adding 2g of hydroxyethyl methacrylate, 3.3g of tripropylamine and 200mL of dichloromethane into a three-necked flask with a mechanical stirring device, the reaction temperature is 0-5°C, and weigh 3.7g of 1-adamantanecarbonyl chloride , and then dissolved it in 60mL of dichloromethane, and dropped it into a three-necked flask within 3 hours. After the dropwise addition, continued to stir for 5 hours, left it standing overnight, and filtered it with suction to obtain a light yellow liquid, which was washed with dilute hydrochloric acid solution ( 1mol / L), NaHCO 3 (1mol / L) solution and distilled water to wash the light yellow liquid (retained liquid is the upper layer), and use anhydrous Na 2 SO 4 Dry, filter, and remove the solvent to obtain a light yellow methacrylic acid-1-adamantanecarboxylic acid ethylene glycol diester solid, whose structural formula is as follows

...

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Abstract

The invention relates to a method for preparing adamantyl-containing unsaturated ester. The method for preparing the monomer comprises the following steps of: simultaneously adding hydroxyl acrylate and tertiary amine into organic solvent for stirring; dissolving adamantanecarboxylic acid chloride in the organic solvent, and slowly dripping the solvent in mixed solution to react at the temperature of between 0 and 5 DEG C; continuously stirring the solution for 5 hours after 3-hour dripping is completed; standing the mixture over-night; filtering the solution; and washing and drying the solution and performing rotary evaporation to obtain the adamantyl unsaturated ester. The preparation method has the advantages of simple and convenient experiment steps, easily controlled reaction process and reduction of possibility of generating side products, and easy realization of industrialization.

Description

technical field [0001] The invention belongs to the field of photosensitive molecular materials, in particular to a preparation method containing adamantyl unsaturated ester. Background technique [0002] Photoresist, also known as photoresist, is a light-sensitive mixed liquid composed of three main components: photosensitive resin, sensitizer and solvent. After the photosensitive resin is exposed to light, the photocuring reaction can quickly occur in the exposed area, so that the physical properties of the material, especially the solubility and affinity, will change significantly. After being treated with an appropriate solvent, the soluble part is dissolved to obtain the desired image. [0003] The technology of photoresist is complicated and there are many varieties. According to its chemical reaction mechanism and development principle, it can be divided into two types: negative gel and positive gel. It is negative gel that forms insoluble substance after light; on...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/753G03F7/004C09D4/02
Inventor 马贵平聂俊姜苹
Owner HANGZHOU INST OF ADVANCED MATERIAL BEIJING UNIV OF CHEM TECH
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